Re: Need help buying a good used sailboat/live-aboard
There are a lot of good boats out there, and it's a buyer's market. But you have to figure out what you want - full keel/fin keel, aft/center cockpit, traditional or modern, lots of teak or none.
Go walk the docks with a cold six pack. Sailors love to talk about their boats - go see what's out there, and try to get a ride on as many as possible.
Also read up the boat inspection threads here and elsewhere. Hire a good surveyor, but the more you know to ask the more a surveyor can teach you.
Good advice above about trying to buy around $60k (plenty for 38-42 feet of boat, perfect for 1-2 people) and saving the rest for upgrades.